Sodium Carbonate → HCID 6410416, compound

HRID 486452Notes

Reaction equation

HRID 486452 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][C:10]1[CH:11]=[C:12]([C:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:19]2[CH2:18][CH:17]=[C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH3:9])[CH:11]=3)[CH2:21][CH2:20]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 13394318HCID 13394318, compound

Product 1

HCID 6410416HCID 6410416, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4.5 parts of 3,6-dichloropyridazine, 5.2 parts of 1,2,3,6-tetrahydro-4-(3-methylphenyl)pyridine, 5.3 parts of sodium carbonate and 72 parts of N,N-dimethylformamide was stirred and heated overnight at about 70° C. The reaction mixture was evaporated and water was added to the residue. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2.1 parts (24%) of 3-chloro-6-[3,6-dihydro-4-(3-methylphenyl)-1(2H)-pyridinyl]pyridazine: mp. 122.2° C. (compound 28).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the residue
  3. extractionThe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe residue was purified by filtration over silica gel using
  8. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2-propanol
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-e69b9578841f4bf69db9789c23764ab2
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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